Like many children, Jesse O’Brien was first captivated by the strange creatures on the Pokemon cards he received for his 7th birthday. And many children and adults enjoy using and sharing cards decorated with cute cartoon creatures with names like Charizard, Bulbasaur and Squirtle.
But then Jesse and his family wondered what was on the rest of the cards – the numbers on the side and the special powers listed at the bottom.
It wasn’t just a map. It was a game.
“My dad said, ‘Well, why don’t we try playing these cards?'” said Jesse, now 11 and a senior at O’Keefe Middle School.
Four years later, these colorful cards have taken Jesse and his family around the world, made him legions of new friends, and won him thousands of dollars as a champion Pokémon player.
In August, O’Brien’s family traveled to Yokohama, Japan to compete in the Pokémon World Championships, where he was the top-ranked North American player in the junior division. In November, both Jesse and his eight-year-old brother Cal will compete in the Pokémon International Latin America Championship in Sao Paulo, Brazil. He will be 12 next month, so he will start playing in the senior division against players aged 16 and up.
His ultimate goal is to win regional, international or world championships as an adult.
“There’s a really good community that Jesse has become a part of playing these tournaments,” said Dan O’Brien, Jesse’s father. “He does have very close friends that he only sees at these tournaments, otherwise he’ll play with them online. They have a unique bond because they are all very, very into it. None of their friends in their hometowns are so excited. I think that’s a big part of what keeps you coming back.”
Jesse O’Brien, 11, keeps his cards close as he plays Pokemon with his brother in the dining room of their Madison home.
You have to catch them all
Squirtle and the other creatures on the cards may be adorable, but the Pokémon card game is complex, sophisticated, and ever-evolving. Two players battle with decks of 60 cards that they have created, using the attacks and special abilities of the characters on the cards to try and defeat each other.
In addition to building the most powerful deck you have ahead of time, players must be able to anticipate and react to the cards their opponent plays.
“You have to be good at math and stuff,” Jesse said. “There’s just a lot of things to figure out and it’s very difficult. You have to watch your stuff. Because if you do something wrong, it can completely change the game.”
Jesse’s mom, Kathy Detmers O’Brien, compared the skills Jesse uses in a match to card counting in poker, keeping track of which cards Jesse has not yet played in his deck and which cards his opponent is playing. Many players build decks modeled after decks they’ve seen win other tournaments. Others will build decks designed to beat those same decks.
“Every deck has a pretty complicated strategy,” said Detmers O’Brien. “If you know a certain deck that someone else is playing and you know the strategy of that deck, you can try to disrupt what they’re doing. It’s a kind of metagame.”
And if that’s not difficult enough, new card sets are constantly released with new strengths and weaknesses that force high-level players to rethink their strategies.
“The game is always changing,” Dan O’Brien said. “New cards almost always change what cards are good and what decks are good. It’s the thing about competitive Pokemon that everyone is always chasing. What is the next best deck? What was good before may no longer be good.”
A large Pokémon trading card signed by Jesse O’Brien’s friends and fellow Pokémon competitors.
A big show
Now imagine you’re tracking all of this in a tournament environment – like a conference center with hundreds of games going on around you at the same time – and the judges are walking between the tables looking for fouls.
For example, at the World Championships in Yokohama, Jesse played seven consecutive 50-minute matches on Day 1. And he did well enough to return for seven more matches on Day 2.
“When you play in a tournament, you have to be very calm,” Jesse said. “If you’re really stressed, you can screw things up because you’re not concentrating.”
Jesse started playing competitive Pokémon games with his family and then went to his local game store, Misty Mountain Games on Cottage Grove Road, to play in local tournaments. (Players accumulate points by winning local tournaments, which lead to invitations to regional tournaments and so on to the World Championship.)
“When I won one of those (local tournaments), I realized I’m not that bad at the game. And then when I made the top 8 for the first time at regionals, I started to think that I really had a good chance to make it to the world championships.”
Jesse has a lucky t-shirt that he wears to every tournament he plays. He said he doesn’t have any pregame rituals, although he usually doesn’t eat much before a tournament, eating half a sandwich for breakfast before eating a full lunch.
But while the stakes are high, Jesse said the players are generally good sportsmen.
“Especially in the early rounds, you’re playing against people who are new to the game,” Jesse said. “And they’re just there to have fun. They don’t expect to go far. But the later rounds get more serious. But people still aren’t mean or anything.’
An example was the World Cup. The last match of the first day was a very close one between Jesse and the Japanese boy. The families of both players looked on, cheering both boys on. Jesse won—and on Day 2, another boy and his family returned to the tournament to support Jesse.
“His dad gave Jesse and Cal cards,” Dan O’Brien said. “They were very generous, especially after Jesse had just knocked their son out of the tournament. It was a really nice experience.”
The day after the tournament ended, the family invited the O’Briens to Sunday brunch. Parents were eating and chatting.
And the two boys were playing Pokemon together.

